WO2018078383A1 - Composition pharmaceutique comprenant du selexipag amorphe - Google Patents

Composition pharmaceutique comprenant du selexipag amorphe Download PDF

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Publication number
WO2018078383A1
WO2018078383A1 PCT/GB2017/053243 GB2017053243W WO2018078383A1 WO 2018078383 A1 WO2018078383 A1 WO 2018078383A1 GB 2017053243 W GB2017053243 W GB 2017053243W WO 2018078383 A1 WO2018078383 A1 WO 2018078383A1
Authority
WO
WIPO (PCT)
Prior art keywords
selexipag
premix
amorphous
acid
depicted
Prior art date
Application number
PCT/GB2017/053243
Other languages
English (en)
Inventor
Dharmaraj Ramachandra Rao
Geena Malhotra
Srinivas Laxminarayan Pathi
Ravikumar Puppala
Anand Ramesh RANKIREDDI
Narayanaswami KOMMULA
Manish Gopaldas Gangrade
Original Assignee
Cipla Limited
King, Lawrence
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cipla Limited, King, Lawrence filed Critical Cipla Limited
Publication of WO2018078383A1 publication Critical patent/WO2018078383A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/20—Nitrogen atoms

Definitions

  • US8791122B2 (hereinafter referred to as the ' 112 patent) discloses different crystalline forms of selexipag including Form - I, II, ⁇ .
  • the ' 112 patent also discloses methods for producing the crystals, and a pharmaceutical composition containing the crystal as an active ingredient.
  • Kollidon VA 64 polyvinyl alcohol, polyethylene glycol, polyol (Mannitol), sodium starch glycolate, colloidal silicon dioxide(aerosil), hydroxypropyl methylcellulose, low substituted hydroxypropylcellulose, hydroxypropylcellulose, methyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, hydroxyethylcellulose, polyvinyl acetate, cyclodextrins, gelatins, hypromellose phthalate, sugars, EUDRAGIT®, such as EUDRAGIT® E PO, and combinations comprising one or more of the foregoing agents.
  • Preferred premixing agents are copovidone and EUDRAGIT®, particularly EUDRAGIT® E PO.
  • the present invention also provides a selexipag premix having enhanced stability, dissolution properties that can be easily formulated into pharmaceutical composition. Furthermore, selexipag may be present in stable amorphous form in the selexipag premix.
  • the present invention provides a complex of selexipag and cyclodextrin.

Abstract

La présente invention concerne des formes à l'état solide de selexipag (formule (I)), comprenant une forme amorphe du selexipag et un pré-mélange contenant du selexipag, des méthodes pour leur préparation, des compositions pharmaceutiques les comprenant et leur utilisation en médecine, en particulier pour le traitement de l'hypertension artérielle pulmonaire. (Formule (I))
PCT/GB2017/053243 2016-10-27 2017-10-27 Composition pharmaceutique comprenant du selexipag amorphe WO2018078383A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN201621036949 2016-10-27
IN201621036949 2016-10-27
IN201621038627 2016-11-11
IN201621038627 2016-11-11

Publications (1)

Publication Number Publication Date
WO2018078383A1 true WO2018078383A1 (fr) 2018-05-03

Family

ID=60302407

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2017/053243 WO2018078383A1 (fr) 2016-10-27 2017-10-27 Composition pharmaceutique comprenant du selexipag amorphe

Country Status (1)

Country Link
WO (1) WO2018078383A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3705115A1 (fr) 2019-03-07 2020-09-09 Alfred E. Tiefenbacher (GmbH & Co. KG) Composition contenant du selexipag

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7205302B2 (en) 2001-04-26 2007-04-17 Nippon Shinyaku Co., Ltd. Heterocyclic compound derivatives and medicines
US8791122B2 (en) 2009-06-26 2014-07-29 Nippon Shinyaku Co., Ltd. Form-I crystal of 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}-N-(methylsulfonyl)acetamide and method for producing the same
WO2016193994A1 (fr) 2015-05-29 2016-12-08 Megafine Pharma (P) Ltd. Selexipag amorphe et son procédé de préparation
WO2017029594A1 (fr) * 2015-08-17 2017-02-23 Dr. Reddy's Laboratories Limited Procédés de préparation de selexipag et de sa forme amorphe
WO2017040872A1 (fr) * 2015-09-03 2017-03-09 Teva Pharmaceuticals International Gmbh Formes à l'état solide de selexipag
WO2017042731A1 (fr) * 2015-09-10 2017-03-16 Lupin Limited Forme amorphe du sélexipag et dispersion solide associée
WO2017109772A1 (fr) * 2015-12-20 2017-06-29 Mapi Pharma Ltd. Forme amorphe du sélexipag
EP3192502A1 (fr) * 2016-01-15 2017-07-19 Sandoz Ag Composition pharmaceutique de selexipag
WO2017121806A1 (fr) * 2016-01-15 2017-07-20 Sandoz Ag Composition pharmaceutique de selexipag
WO2017168401A1 (fr) * 2016-04-01 2017-10-05 Honour (R&D) Procédé de préparation de dérivés de diphénylpyrazine

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7205302B2 (en) 2001-04-26 2007-04-17 Nippon Shinyaku Co., Ltd. Heterocyclic compound derivatives and medicines
US8791122B2 (en) 2009-06-26 2014-07-29 Nippon Shinyaku Co., Ltd. Form-I crystal of 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}-N-(methylsulfonyl)acetamide and method for producing the same
US8791122C1 (fr) 2009-06-26 2014-07-29
WO2016193994A1 (fr) 2015-05-29 2016-12-08 Megafine Pharma (P) Ltd. Selexipag amorphe et son procédé de préparation
WO2017029594A1 (fr) * 2015-08-17 2017-02-23 Dr. Reddy's Laboratories Limited Procédés de préparation de selexipag et de sa forme amorphe
WO2017040872A1 (fr) * 2015-09-03 2017-03-09 Teva Pharmaceuticals International Gmbh Formes à l'état solide de selexipag
WO2017042731A1 (fr) * 2015-09-10 2017-03-16 Lupin Limited Forme amorphe du sélexipag et dispersion solide associée
WO2017109772A1 (fr) * 2015-12-20 2017-06-29 Mapi Pharma Ltd. Forme amorphe du sélexipag
EP3192502A1 (fr) * 2016-01-15 2017-07-19 Sandoz Ag Composition pharmaceutique de selexipag
WO2017121806A1 (fr) * 2016-01-15 2017-07-20 Sandoz Ag Composition pharmaceutique de selexipag
WO2017168401A1 (fr) * 2016-04-01 2017-10-05 Honour (R&D) Procédé de préparation de dérivés de diphénylpyrazine

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
"Amorphous Selexipag Formulations", RESEARCH DISCLOSURE, KENNETH MASON PUBLICATIONS, HAMPSHIRE, UK, GB, vol. 618, no. 27, October 2015 (2015-10-01), pages 2, XP007144400, ISSN: 0374-4353, [retrieved on 20150909] *
BAGHEL, S. ET AL.: "Polymeric Amorphous Solid Dispersions: A Review of Amorphization, Crystallization, Stabilization, Solid-State Characterization, and Aqueous Solubilization of Biopharmaceutical Classification System Class II Drugs", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 105, no. 9, 23 January 2016 (2016-01-23), pages 2527 - 2544, XP055430383, ISSN: 0022-3549, DOI: 10.1016/j.xphs.2015.10.008 *
HANCOCK, B.C. ET AL.: "What is the true solubility advantage for amorphous pharmaceuticals?", PHARMACEUTICAL RESEARCH, vol. 17, no. 4, 2000, pages 397 - 404, XP009086748, ISSN: 0724-8741, DOI: 10.1023/A:1007516718048 *
SIX, K. ET AL.: "Thermal Properties of Hot-Stage Extrudates of Itraconazole and Eudragit E100: Phase separation and polymorphism", JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, vol. 68, no. 2, 2002, pages 591 - 601, XP019254152, ISSN: 1572-8943 *
VAN DEN MOOTER, G.: "The use of amorphous solid dispersions: A formulation strategy to overcome poor solubility and dissolution rate", DRUG DISCOVERY TODAY: TECHNOLOGIES, vol. 9, no. 2, 2012, pages e79 - e85, XP055317903, ISSN: 1740-6749, DOI: 10.1016/j.ddtec.2011.10.002 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3705115A1 (fr) 2019-03-07 2020-09-09 Alfred E. Tiefenbacher (GmbH & Co. KG) Composition contenant du selexipag

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